| 03 Jul 21 | r02        | Humble LionsHumble Lions | 0 - 1 | Mount Pleasant FAMount Pleasan |
| 03 Jul 21 | r02        | Molynes UnitedMolynes Unite | - | UWIUWI |
| 03 Jul 21 | r02        | DunbeholdenDunbeholden | 0 - 2 | Waterhouse FCWaterhouse FC |
| 05 Jul 21 | r02        | Harbour ViewHarbour View | 1 - 1 | CavalierCavalier |
| 06 Jul 21 | r02        | Tivoli GardensTivoli Garden | 1 - 0 | Arnett GardensArnett Garden |
| 06 Jul 21 | r02        | Vere UnitedVere United | 1 - 0 | Portmore UnitedPortmore Unit |
| 23 Jan 22 | r02        | Humble LionsHumble Lions | 2 - 2 | Tivoli GardensTivoli Garden |
| 23 Jan 22 | r02        | Mount Pleasant FAMount Pleasan | 1 - 0 | Harbour ViewHarbour View |
| 24 Jan 22 | r02        | CavalierCavalier | 0 - 3 | Waterhouse FCWaterhouse FC |
| 24 Jan 22 | r02        | DunbeholdenDunbeholden | 3 - 0 | Montego Bay UnitedMontego Bay U |
| 25 Jan 22 | r02        | Portmore UnitedPortmore Unit | 1 - 2 | Arnett GardensArnett Garden |
| 25 Jan 22 | r02        | Molynes UnitedMolynes Unite | 0 - 1 | Vere UnitedVere United |